Silver Nanoparticles Decorated with PEGylated Porphyrins as Potential Theranostic and Sensing Agents

Silver nanoparticles (AgNPs) stand out over other metal nanoparticles thanks to their peculiar bactericidal and spectroscopic properties. Tunability of the AgNPs chemical–physical properties could be provided through their organic covalent coating. On the other hand, PEGylated porphyrin derivatives are versatile heteromacrocycles investigated for uses in the biomedical field as cytotoxic and tracking agents, but also as sensors. In this work, an easy multi-step approach was employed to produce coated silver nanoparticles. Specifically, the AgNPs were functionalized with 5,10,15-[p-(ω-methoxy-polyethyleneoxy)phenyl]-20-(p-hydroxyphenyl)-porphyrin (P(PEG350)(3)), using chloropropanethiol as a coupling agent. The P(PEG350)(3) was structurally characterized through MALDI-TOF mass spectrometry, NMR spectroscopy and thermal analyses. The functionalization of AgNPs was monitored step-by-step employing UV-Vis spectroscopy, dynamic light scattering and thermogravimetric techniques. HRTEM and STEM measurements were used to investigate the morphology and the composition of the resulting nanostructured system (AgNP@P(PEG350)(3)), observing a long-range alignment of the outer porphyrin layer. The AgNP@P(PEG350)(3) combines the features of the P(PEG350)(3) with those of AgNPs, producing a potential multifunctional theranostic tool. The nanosystem revealed itself suitable as a removable pH sensor in aqueous solutions and potentially feasible for biological environment applications.